#1
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopFri, Nov 13, 2026Tickets from $69
Theater of the Mind
Downtown, the Loop & West Loop
Theater of the Mind at Reid Murdoch Building – 333 N LaSalle.
Limited Run
Date night in West Loop, Chicago Halloween Weekend 2026
4 picks
The 4 best date night picks in West Loop, Chicago over Halloween Weekend (Oct 30 – Nov 1)
- Theater of the Mind — Fri, Nov 13 · Tickets from $69 · Downtown
- Kokandy Productions Jekyll & Hyde (Chicago) — Fri, Oct 30 7:00pm · Downtown
- Drunk Shakespeare: Drunk Dracula (21+ Event) — Fri, Nov 6 7:00pm · Downtown
- The Winter's Tale — Sat, Nov 7 7:00pm · Downtown
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West Loop#1Fri, Nov 13, 2026 · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West Loop#2
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West LoopFri, Oct 30, 2026 · 7:00pm
Kokandy Productions Jekyll & Hyde (Chicago)
Downtown, the Loop & West Loop
Kokandy Productions Jekyll & Hyde (Chicago) at Broadway Playhouse at Water Tower Place.
Limited Run
#2Fri, Oct 30, 2026 · 7:00pm · Limited Run
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West LoopKokandy Productions Jekyll & Hyde (Chicago)
Kokandy Productions Jekyll & Hyde (Chicago) at Broadway Playhouse at Water Tower Place.
Add to calendar#3
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopFri, Nov 6, 2026 · 7:00pm
Drunk Shakespeare: Drunk Dracula (21+ Event)
Downtown, the Loop & West Loop
Drunk Shakespeare: Drunk Dracula (21+ Event) at The Lion Theatre.
Limited Run
#3Fri, Nov 6, 2026 · 7:00pm · Limited Run
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopDrunk Shakespeare: Drunk Dracula (21+ Event)
Drunk Shakespeare: Drunk Dracula (21+ Event) at The Lion Theatre.
Add to calendar#4
Chicago Shakespeare Theater, 800 East Grand Avenue on Navy Pier, Downtown, the Loop & West LoopSat, Nov 7, 2026 · 7:00pm
The Winter's Tale
Downtown, the Loop & West Loop
The Winter's Tale at Chicago Shakespeare Theater.
Limited Run
#4Sat, Nov 7, 2026 · 7:00pm · Limited Run
Chicago Shakespeare Theater, 800 East Grand Avenue on Navy Pier, Downtown, the Loop & West LoopAbout this list
Stumblday's hand-checked ranking of the best date night in West Loop, Chicago, Downtown, the Loop & West Loop over Halloween weekend 2026 (Oct 30 – Nov 1): 4 picks.
